The young girl could feel the lukewarm air brush against her shoulders; summer decided to have slightly chiller nights. She sighed, knowing to get an actual job but none provide as much money as the one she choose. Ruby needed that salary.

If any of her friends knew what she was about to do, they'd… Ruby gave her head a firm shake. She made this decision on her own; no one forced her, no one threatened her, and no one said she had to. Silently repeating that to herself, Ruby did one final look-over at her ensemble.

It was modest; a black lacy off-the-shoulder top, matching the trimmings on her black transparent thigh-highs. A red and pink rose-patterned black miniskirt with black ballet flats to showcase her legs. Her brand new white chain purse completed the look. It was all a bit too girly for her tastes, but Ruby didn't wish to be recognizable — to the point where she grew her hair out over the past few months and dyed the tips red. She even made an attempt with makeup and curling her hair. She had the burns to prove it.)

Ruby took a deep breath and went off, hailing a taxi to possibly the worst place in all of the city — the red light district.

Her flats left faint hollow clicks against the concrete. Ruby wrinkled her nose a little from foul smells. Countless gaudy neon signs blinded her. She would've gone somewhere else, but knew she wouldn't be recognized, or seen, by anyone she knew in a place like this. She looked around. How am I suppose to attract attention…? Lost in deep thought, she didn't realize how much attention she was already attracting. Ruby let out a shriek as she felt a slap against her backside.

Turning around, she found herself surrounded by five men. Each was dressed in a black suit with a matching hat and shoes, red sunglasses, and a red tie, with a small amount of variation to distinguish them. All of them had black hair with two having a black mustache as well. They all also seem to have the same skin tone.

"C-Can I help you?" Ruby asked, smiling nervously and felt beads of sweat drip down on the nape of her neck.

One of the men flashed her a nasty sneer. "How much?"

"Oh! Uh…um…w-well that d-depends on—"

"Nice try boys, but I already made her an offer she couldn't refuse."

Ruby turned her head to the direction of the voice. Standing before her was a tall and slender man. He stood out mostly because of his white single-breast jacket; the rest of his ensemble black with a gray tie. His bright orange hair well-groomed and slicked back, giving an air of a professional. Ruby's silvery eyes meet emerald ones, forgetting her current situation. But a gruff voice quickly brought her back.

"The hell you talking about Torchwick!? I didn't see you offer her shit!"

"Okay, you're right — I didn't." The man admitted smirking, momentarily breaking eye contact with the young girl to address the other man. "And just what were you going to offer, might I ask?"

"Five hundred."

"For an hour?"

The black-clothed man sneered. "That's right."

"You truly are a cheapskate." He turned back to Ruby. "Hello Red. Roman Torchwick at your humble service. And I'll offer you a grand per hour."

While the group of men voiced their complaints, Ruby stared at Roman, dumbfounded. Will he really pay you…? The back part of her mind questioned. A rush of sudden bravery washed over her. She held out her palm. "Two grand, in cash…upfront?" She dared asked.

"Two grand it is then." Roman agreed, smiling as he reached for his wallet. Pulling out a few hundreds and fifties — along with twenties and tens here and there — he placed the money into her small hand. Ruby counted it to be sure. Discovering he truly did pay all two grand, she tucked it all into her purse. She looked back up at Roman and gave a nod. "Okay, where do you want to go?"

He grinned and offered her his arm. "I know a place."

Taking his arm, Ruby let him lead her on, leaving the group of men to their own misery and groans.

Staring. That's all they did for nearly the past hour — staring. Roman stared at the young girl from the leather couch. Ruby stared out the window — on the far side opposite of the room (and from Roman) — from the tenth floor boutique hotel room. It was rather luxurious actually; open and spacious with a king-size bed. Expensive no doubt, albeit Ruby seemed more interested in the blinking traffic light down below her.

"Are you afraid of me, Red?" Roman finally broke the brittle silence. Ruby stiffened, mechanically shaking her head. "N-No…! I-It's just that I…I never really done this before in a p-place like this and…a-and…" She grew more flustered with every word, wishing she kept quiet.

Seeing her so flustered made Roman's pants tighten. He wanted nothing more than to feel her with his own skin. He cursed under his breath at the fact they were both still heavily dressed.

That was about to change…

Getting up, Roman walked over to Ruby and turned her to face him. She looked up at him confused. "Wha—?" She couldn't finish because at that moment he had her lip-locked.

"Mmm…" She muffled as Roman wrapped his arms around her. He rested his hands on her lower back. Unable to resist, they drifted lower to her soft rear. Even through the silky fabric he could feel how firm and plump it was. He couldn't resist any longer and squeezed it firmly causing her to break the kiss and throw her head back and cry out. Roman smiled. Her sounds were absolutely incredible, and he wanted to hear more of her sweet voice.

His eyes flickered to her face. She was definitely hesitant and embarrassed. "I-I've never..." Ruby couldn't finish. But he knew what she meant. He pushed his face into her neck and inhaled her rosy scent, earning himself a slight sigh. "I'm not stopping here…" was all he whispered. She grew quiet, and he heard her take a deep breath.

"I'm scared..." She finally admitted.

Roman brought his head back up, noticing her alarmed expression.

"Why's that?" He asked, stroking her hair comfortingly. She looked at him and then away again.

"W-What if… What if I don't 'respond' the 'right way'…or I…I can't satisfy?" She asked worriedly.

Roman chuckled. And she looked at him slightly annoyed.

"What?" She grumbled.

"Don't worry about that. It doesn't essentially matter to me. I mean I'm not exactly what you would call a saint." He explained. Ruby blinked, but wasn't shocked. He didn't exactly give off that vibe. Roman kissed her passionately again. "Is that enough reassurance?" He smiled. She blushed and shyly nodded. But even though he was considerate enough, she was still nervous. Roman read her expression.

"I'll teach you many things. I'll bring you to your sexual peak, Red." He whispered seductively.

Before she could respond, he picked Ruby up bridal style and carried her over to the bed; her flats slipped off, falling to the ground. His strength surprised her, and almost marveled her. He set her down gently, then stood up to undress himself. He kicked off his dress shoes and pulled off his socks and coat, tossing them to the floor. Then he untied his tie, slipped it off and unbuckled his belt around his dress shirt, undoing the buttons to reveal his defined upper body. He kept his pants on for the time being. Ruby stared at him in wonder.

Roman buried his face into her neck, breathing in her scent again as he firmly embraced her petite form. Ruby, arms wrapped around his back, slowly closed her eyes from the heated sensation, warming her body. She couldn't stop the small "eep" escaping her lips as Roman suddenly placed small kisses on her shoulders as his arms squeezed her closer. His lips travelled up her neck and nestled under her ear; hot breath ghosting over. "Ready…?"

He was still giving her a chance to turn away. Ruby took in a deep breath and nodded again, knowing very well she was only half prepared. He chucked and nibbled her ear, running one hand up underneath her top and rest upon her breast. "So it does have a built-in…"

Ruby's face burned. "Hey!"

Roman laughed and kissed her cheek. "I meant no offense Red. Just making a verbal observation. But on a more serious note, try not to have outbursts like that in the future — you'll kill the mood." With that, he slowly began pulling off her top, exposing her smooth, pearly white, skin to his gaze.

Once Ruby's top was over her head, he tossed the article of clothing to the floor. As soon as he did, he licked her neck and trailed downward to her breasts. Her breasts were bigger than he imagined, but just as well rounded and perky as he guessed. Both hands ran over her soft breasts, bumping over the erect nipples, sensitive to his touch. Ruby let out a small moan, feeling him pinch her nipples. Her breathing became more heavy and her vision hazy, glancing down at the older man teasing her. Roman's eyes moved from her chest to her delicate face.

She was beautiful, he decided. Brilliant silver eyes — like the moon itself — with long eyelashes that couldn't possibly be fake. Thick, rich, dark hair tinted red, cascading down to her waist and glossed pale pink, heart-shaped, lips; slightly swollen from the affections moments before. Ruby had an innocent beauty that not even he denied. Roman reached out to tuck her hair behind her right ear and caressed her cheek.

Ruby stared up at him in confusion. Before any of this she assumed it would be quick and extremely rough, but this man truly surprised her. Granted, they both knew it wasn't really love — only possibly a one-night stand, nothing more and nothing less. I guess that doesn't mean he can't enjoy himself…or at least get his money's worth… She thought, letting out a small sigh. Then seemingly out of nowhere, Roman quickly leaned in and tenderly kissed her.

Wide-eyed, the young girl's cheeks turned pink by the sudden action, albeit soon relaxing. Fondling her breasts, he licked her lower lip. Hesitantly she opened her mouth, her tongue gingerly meeting his. Having little to no experience, Ruby didn't mind Roman taking dominance. However she abruptly broke the kiss, letting out a surprised gasp.

Unaware and distracted by the kiss, Roman had sneaked one hand underneath her skirt, pressing his middle finger against her panty-covered folds. Face flushed, Ruby looked at him embarrassed. He smiled, continuing to stroke against the silky fabric. "You know, Red… You made the smart move on wearing a skirt, they're much easier to remove than pants." With two fingers, he began pulling off the said clothing. Ruby lifted up her hips so Roman could fully remove it. The skirt dropped to the floor, joining her lacy top; her thigh-highs soon followed after.

Roman gazed upon the innocent maiden before him. Only lacy black panties shield her most sacred virtue. Her arms hugged her chest, her legs squeezed together. His eyes never stayed in one place for too long for two reasons: one, he didn't want to make her feel uncomfortable. Two…well he just kept finding places on her delicate figure that were better than the last. It bewildered him to think this timid girl, scared out of her mind from being surrounded by half a dozen strangers earlier, was now serene.

Letting out a chuckle, Roman sat up, shrugged off his shirt and leaned in. Then his hand searched and found hers and guided it up to his chest. For a moment Ruby simply felt the beating of his heart. Unconsciously, she sat up in front of him and gingerly traced her hand along his pectorals. Roman remained still so that she could exploit her curiosity, along with her getting used to the feeling of him. Her hand continued to slid across his skin, slowly bringing up her other hand. She looked down and used her fingers to trace the contour of his abs. They were smooth and define, towards the bottom they almost formed a v-shape that guided her to his lower region.

But then she noticed a slight bulge forming and pushing against the fabric of his pants. Her cheeks flushed, but she was visibly curious. She moved her hand to the bulge and rubbed her palm against it as gently as she could. Roman grunted at the slight pleasure, catching Ruby off guard. But as he slowly shook his head, she guessed that his outburst was out of enjoyment not pain. So she resumed. This time she gripped it lightly and rubbed it a little more confidently, and she once again heard him grunt before he stopped her motions.

She looked at him, surprised that he stopped her. But he smiled and shook his head.

"I'm teaching you this time." He replied pushing her back onto the bed and climbing on top of her. As he stared down at her, Ruby began to fidget while trying to adjust to a more comfortable position. He exhaled lustfully, enjoying her anticipation.

Being underneath the half naked man above her was becoming more and more nerve-racking with every passing second. But Ruby wasn't going to push him away. She didn't want to, even if she was still nervous. She rubbed her thighs together. Her body was starting to feel a desperate need for friction, but she didn't know how to tell Roman without embarrassing herself. Luckily he caught on and smiled perversely.

"Finally giving in?" He teased. She grumbled to herself but instantly stopped when he started taking her panties off. The feeling of his hands against her thighs felt tingly and this time she wasn't going to stop him from removing them. Ruby suddenly felt self-conscious, and tried to cover herself up, only to have Roman push her hands away.

"Don't worry. You won't care about that soon…" He smiled.

He brought his head down and trailed kisses all the way from her mouth to her lower abdomen. As his hot lips fluttered against her skin, she unknowingly bucked her hips. She closed her eyes and grabbed his shoulders tightly, and absentmindedly pushed him further down.

"Please...?" She heaved.

Roman complied and brought his head between her legs, and started kissing her inner thighs until he came to her most sensitive spot. Using his index finger, he began to rub her folds. The pleasure was a new feeling to Ruby and she moaned and threw her head back.

"You want more Red?"

Ruby released another breathless sigh and nodded intently.

Roman quickly lowered his head back in between her thighs. His breath ghosted over her, sending shivers down Ruby's spine. She rolled her hips, signaling to continue. He kissed her briefly and began to teasingly trace his tongue around her folds causing her vision to blur. She brought her hands down and gripped his hair as he caressed her. "Mmmh... Roman…" She moaned. His hands held firmly onto her thighs to stop her from bucking her hips too wildly. He pushed his tongue harder against her folds. Her taste was strangely addicting — sweet with a hint of bitterness, a flavor that excited him.

Ruby's grip in his hair tightened as she felt a strange new sensation building up in the pit of her stomach. "Roman…I-I…" She sighed. He ignored her and focused onto her swollen clit, licking and sucking on it hungrily. She moaned loudly, no longer caring that he can hear her. The build in her stomach heightened and her body was begging for a release. She looked for the right words to tell him but…

She exhaled softly. "Please… Ah… D-Don't stop..."

Hearing her words pushed him to nibble her clit and pull it with his teeth excitedly. "N-No... Roman...!" Ruby panted loudly. She knew she could longer hold it back anymore. Her body jerked and tensed up, and her grip on his hair became excruciatingly tight as she came to her release. She cried his name over and over as small gush of her release flowed into his mouth. He moaned and selfishly lapped up and swallowed every drop until she ceased. Her hands loosened his hair and fell to her sides exhausted.

"S-Sorry if I…hurt your head…" She apologized, panting.

Roman lifted his head up and licked his lips. "It takes more than that to hurt me, Red." He replied, kissing her. He cupped her face and pulled her close. Twisting their tongues together, Ruby tasted something foreign. Her face burned realizing it was her own taste.

Roman grunted. The discomfort of his hard member tugging at the fabric of his pants was becoming unbearable. He pulled away. He removed his pants' belt, then moved to the edge of the bed and slid his pants off, now only wearing his boxers. With more room for his erection he sighed in relief, but was still a bit frustrated at the slight resistance that still held it. Suddenly he felt Ruby's arms wrap around him as she pressed her body against his back. Her hair tickled his sides.

"Does it hurt?" She asked innocently resting her head on his shoulder. He felt her hot breath against his back, and smiled.

"Not really." He replied turning around and pulling her close to him. After laying her back on the bed one last time, his hands started to massage her soft breasts. Ruby moaned as he pinched her erect nipples again and teased them roughly. His head lowered and enveloped one of her nipples into his mouth as he continued to knead the other. Suckling on the tender bud, he swirled his tongue against it and loved how Ruby continuously cried out his name.

Ruby could feel his erection brush against her inner thigh and throb. Roman pulled away, and decided to stop denying his impulses any longer. Finally he gripped his boxers and pulled them off earning himself a gasp from Ruby. He was now fully revealed, just like Ruby. She stared at his member. It was bigger than she imagined, and her nerves were returning slowly. He grabbed his erection and positioned himself in front of her. The searing and considerably large flesh prodded her opening as he rubbed himself against her folds. Another gasp escaped her lips. But Roman's expression grew serious.

"This might hurt, if it does… Hold onto me…" He whispered, kissing her forehead. Ruby nodded shyly and wrapped her arms around his back tightly. He eased his way into her, taking it slow and looking at her face for any signs of pain or discomfort. But he found it difficult to go slowly because of how the inside of her felt. She was so warm as she molded around him, and he had to use every muscle in his body to keep from slamming into her and fucking her relentlessly. About halfway inside he felt a resistance. It was both a good and bad thing. On the upside she wasn't lying and actually is a virgin, but on the downside...

"Like I said Red, hold onto me…" He repeated. Her grip on his back tightened and she nodded, preparing herself.

With a quick thrust he pushed through her hymen and buried himself deep inside. Instantly she squeezed him in a jolt of pain, and shut her eyes, swearing under her breath. Roman kissed her neck and every spot on her face gently hoping it would help. "Sorry about that." He whispered. She took a moment to let the brief pain leave her system. "It wasn't…as bad I thought it would be…" She sighed relieved. Roman smiled and kissed her. "That's good Red. It's good that you're strong like that…" He replied. To his surprise she smiled. "Because I have someone who teaches me." She whispered giving him a peck on his cheek. He was shocked. "Damn Red, you know what you're doing…" He grinned.

She nodded her head, giving him the "okay" to move.

He started moving slowly; making sure she got used to his size being inside of her. He pulled out and pushed back into her, restraining his hips. When her moans grew louder and less filled with pain he gradually increased his pace. "F-Faster…!" She pleaded, kissing him. Roman complied and his thrusting increased. They moaned into each other's mouths at the pleasure sweeping over them. Ruby broke the kiss and tried to catch her breath. "Roman…" She moaned loudly. He wanted to hear more of her sounds so he licked along her jugular and sucked on it, knowing it would leave a mark. He smirked upon hearing her whimper.

He groaned as he pulled her hips into his erection for deeper penetration. Ruby's voice rose higher and higher with every passing thrust. She could feel every inch of him slide in and out of her in carnal desire. "Red…" He moaned breathlessly. She gripped the sheets of the bed. Her lust only increased as he pounded into her, and she could feel the tingles and excitement building up between both of them.

She yelled. "M-More...!"

Hearing those screams made Roman even harder, and he found himself building up and getting closer to release. He grunted laying his body down on top of hers. He felt her nipples brush up and down against his chest, and their lips touching but never quite kissing. Roman groaned as Ruby decided to kiss his neck like he did hers. She nipped at his lower jaw and kissed him over and over again feeling his tongue against hers.

She too could feel her release getting closer. Both were in need for more intensity, so Roman reluctantly pulled out. Ruby sighed in frustration, but stopped when he sat up and pulled her onto his lap. He gripped her waist tightly.

"Wrap you legs around me." He whispered. Ruby did as he asked, and then she lowered herself back onto him.

He slammed upwards and pulled her hips down at the same time. She yelped pushing her head into his shoulder. Roman's torso was rubbing relentlessly against her breasts, and the new position instantly made it harder for both of them to last. Ruby tightened her arms around him and they stared deeply into each other's eyes. Several breathless moans escaped their mouths and echoed through the room.

Consumed by pleasure, he rolled her onto her back again and she instantly gripped the sheets. Ruby's body tensed up first and she arched her back. Roman felt her walls clench tightly around him, squeezing him relentlessly before her release hit her even harder than before. He continued thrusting into her through it, not easing up in the slightest.

"Roman…!" She cried.

"Red…!" He yelled.

Ruby felt warmth deep inside her. The release felt so good that Roman's hands gripped the sheets and he pressed his head onto the bed next to hers. His breath ghosted Ruby's neck causing her to shiver. He filled her up inside and she loved the feeling. There was so much that some of it managed to escape her and trickle onto the bed, but they didn't care.

He regained his senses faster than her. He slowly pulled out of her. She panted heavily as he watched her chest rise and fall. Seeing her like that was almost enough to make him go another round. After a few more moments she sat up. Roman cupped her cheek and kissed her.

"Are you alright?" He asked grinning. She blushed and nodded.

"Yes…" She whispered.

He kissed her again. Then he stood up and started to get dressed. Ruby was about to until she noticed that it was almost eleven. "Looks like our two hours are up Red. Too bad though, I wanted to go another round. I didn't get a good enough taste of my new favorite candy." Roman said, lighting a cigar. She blinked hard.

"Your new favorite candy?" She blushed, embarrassed that he would refer to her that way.

"You should get 't to catch a cold now would you?"

Ruby nodded and tried standing up but fell to her knees when she felt excruciating pain between her thighs.

"Ow!" She winced, rubbing her rear. She heard Roman chuckle.

"What the—? Roman! Why are you laughing? This isn't funny. I don't think I can stand up! When I tried to, my…down there just hurts!" She stuttered.

"Whoops… Well, I think you'll feel better in a few days. I guess it's my fault. I was so turned on by you that I may have pounded into you a bit too roughly." He grinned triumphantly. Ruby's entire face grew red with anger.

"TORCHWICK!"

Ruby was quiet in the taxi drive home. She was still mortified by what she did ten minutes ago.

"Let me guess, first time?"

Silver eyes looked at the rear view mirror. Two dark brown irises glanced at it before returning to the road. "Well…?"

"…Yes." Ruby replied, faintly blushing. "But how did—?"

"Lady, trust me. I've been living on the streets for so long that I can just tell. So who was it with? Quicksilver? Jockstrap? Prissy finally?"

"No, no, and no…" She answered, wondering if those were their actual nicknames or ones the cabbie made up. "Wait, what makes you think I want to talk about it at all!? With you!?"

"Who else are you gonna tell? Your friends? Your family? Your pet?" The cabbie said. "You gotta tell someone. Even if that someone is just some random cabbie like myself. So spill — how much from who?"

Ruby took in a deep breath. The cabbie was right; she had to tell someone, she wouldn't be able to bottle this up. "Two grand upfront from…Roman Torchwick."

"The Conman!?" The cabbie blurted out, genuinely surprised. "You gotta be kidding me!"

"N-No!" Ruby grew confused. "Why…?"

"Because he never goes over seven hundred and never pays up front in full. Would call him "The Swindler" if it wasn't for that charisma and confidence. Kinda relieved it was him…even if he is a bit of a cheapo. 'Frugal' ma sweet combat boots…" The cabbie muttered, with that last statement sounding more like thinking out loud.

"H-How do you know for sure!?" Ruby almost demanded to know.

"'Cause he sometimes does a quickie right there in that very spot you're sittin' on." Came the answer. "Dude's relentless and picky. Not to mention it takes time out of my own work schedule to comfort some of the ladies he leaves behind along with cleaning up after—"

"Okay, okay!" Ruby cried out, face red and covering her ears. "Please just…stop talking about it…"

"Sorry."

They rode in silence for a pregnant pause.

"He said he would see me again…"

The cabbie looked at Ruby through the rear view mirror again. "That right?"

She nodded.

"Great, that means I have to be in the middle of all this..."

"Huh…?"

"You don't know? If anyone in this area wants to tell anyone something without anyone else knowing, they come to me. People either trust me or not because of it."

"Ohhhhhh…"

"By the way, why did you did what you did?"

Ruby nervously furrowed her eyebrows. "F-For money?"

"Obviously, but why?"

She went quiet and hung her head. "For bills… I couldn't ask my friends…or my dad…and my sister recently broke her arm from a bar fight and what with trying to earn my degree…"

"Mm..." The cabbie nodded. "Life isn't a fairytale for you right now, is it?"

"Yeah…but we all strive to make it better."

"Ain't that the truth." The cabbie agreed. "Tell you what — I'll help you out."

Ruby looked back up. "Really?"

"Why not? You're a nice lady. Pretty sure this prolly won't be your last time from what you're explaining to me. And I pretty much know everybody in this entire city so I can help you with clients, what areas to avoid, who to avoid…and one more thing…"

Ruby listen attentively. "Yes?"

"You sure you wanna keep doing this? It's dangerous. And I don't mean just physically. You could end catchin' something you're not gonna want and that medicine is as expensive as hell."

"Actually…I'm one of the handful of people that are…sorta immune to AIDS."

"Seriously? Damn, sure lucked out didn't you? You basically just have to worry about rape. Speaking of which, if some lowlife does do that, call me immediately and I'll personally take care of it."

Ruby felt a chill down her spine when the cabbie said that, but nodded. "You're a pretty cool girl."

The cabbie grinned. "Been a while since someone guessed my actual gender. Haven Grey, atcha' service Miss. Looking forward to workin' with ya."

Ruby laughed. "Likewise."

Heyo!

Uh...yes, I legitimately wrote this. I turned eighteen on the nineteenth (Eeeeeey!) so...yeah. Kinda exploited on smut here.

It came to me after reading a few other RWBY lemons. While it was enjoyable (with a few of Ruby FF harems...), it got kinda boring and are super unrealistic. So I going out on a limb here. PM or review to make requests and I'll see what I can do. Basically you can pretty much pair Ruby up with anyone (except Yang...). I'm having an idea for Ruby's next hook-up (and I have seen NO ONE do this pairing yet), and uh...yeah... I made it an AU where some people, like Ruby, have a higher immune system to avoid AIDS, while there's medicine for everyone else less fortunate. Did that for two reasons: one, to avoid some complications in actual reality, and two, refer to the first reason.

Basically I'll write this whenever possible. I totally believe seduction and foreplay is what get people turned on, so...yeah...

Added an OC for the halibut.

So as always, Favorite, Follow, or Review or whatever!

Peace!